Lucky for us, Loudon Wainwright III is only “so damn happy” on an infrequent basis.   The singer-songwriter-humorist-satirist-actor (is that enough of a multi-hyphenate for you?) posited the question “Is it necessary to feel like shit in order to be creative?” He arrived at the final answer “yes!” but prefaced it with “unless you’re J.S. Bach.” Over the course of 91 songs on four CDs and another 38-plus on DVD, Shout! Factory’s new box set 40 Odd Years (82663-12189, 2011) – dig the double meaning of that title! – invites listeners on a journey through the singular world of the thankfully malcontented Wainwright.  What does such a trip entail?  Prepare yourself for songs alternately emotional and humorous (and frequently both!) reflecting on the subject’s favorite themes: childhood, parents, children, booze, death, the passage of time, and of course, show business.

40 Odd Years accomplishes one of the rarest feats of all, as it’s suitable for both the new fan seeking an entrée into the artist’s catalogue and the diehard looking for unheard rarities.  All phases of Wainwright’s body of work are covered, beginning with 1970’s self-titled debut for Atlantic Records and ending with 2009’s High Wide and Handsome: The Charlie Poole Project.  Even after taking in all 91 audio tracks, though, the question remains: Who is Loudon Wainwright III?  The artist abbreviated as LW3 has sometimes been compared to Randy Newman, and like Newman, had his biggest commercial success with an atypical song.  (For Newman, it’s the oft-misunderstood “Short People,” while Wainwright’s success came via the novelty-style “Dead Skunk.”)  But whereas Newman’s songs are almost exclusively sung in character, usually by a deviant of one stripe or another, Wainwright’s character is most often his own.

Upon the release of that 1970 debut, he was hailed as a “new Dylan.”  But who, then, wasn’t?  The comparison isn’t completely off-the-mark, given Loudon’s pinched, somewhat nasal voice as he accompanied himself on acoustic guitar.  But the lyrical content of Wainwright’s songs couldn’t be more far-removed from the favorite son of Hibbing, Minnesota.  Having been born to an affluent family (his father wrote the column “The View From Here” in Life) and raised in a New York suburb, Wainwright hailed from a different place.  Liza Minnelli was even a classmate of his!  In his terrific 2004 speech “My Cool Life: The Singer-Songwriter as Autobiographer” (reprinted in 40 Odd Years’ booklet), Wainwright name-checks classic Broadway songwriting teams, and in fact, he signed as a young songwriter to Frank Music, the publishing firm owned by Frank Loesser of Guys and Dolls and How to Succeed in Business Without Really Trying fame.  (It’s now owned by Paul McCartney.)  His understanding of the classic Tin Pan Alley and Broadway songwriting idiom is reflected in the considered structure and craft of his songs.  But the siren song of the burgeoning hippie and folk movements also called to Wainwright, a professed fan of Leadbelly, Tom Lehrer, Hank Williams and Louis Prima.  Talk about diverse influences!

The Shout! box covers those 40 odd years in chronological order, and adds one disc of unreleased and rare material as well as a 3+ hour DVD that may be the most comprehensive “bonus DVD” yet in a box set of this kind. Hit the jump to find out how well 40 Odd Years represents the music of a true eccentric, Loudon Wainwright III.

What’s initially striking about the package is that it’s a throwback (like Shout! Factory’s 2009 Richard Thompson box Walking on a Wire) to the Rhino box sets of yore, housed in a sturdy 12 x 6” box containing a large booklet and all its discs in jewel cases.  This format makes a welcome return and reminds one of the days when smaller wasn’t everything, and a deluxe box set didn’t mean “LP-sized with lots of swag.”

All sides of Wainwright’s talent are on full display even if every favorite song may not be included. (The singer compiled the set himself alongside his devotee, director Judd Apatow.)  There’s much ado about family, youth and children, which is no surprise when considering Wainwright’s own lineage.  He’s a direct descendant of New York colonial governor Peter Stuyvesant, had a famous father, and even has famous children following in his footsteps, singer/songwriters Rufus Wainwright, Martha Wainwright and Lucy Wainwright Roche.  Two of his wives were singers Kate McGarrigle and Suzzy Roche, both members of prominent musical families themselves.  Younger sister Sloan Wainwright is another singer/songwriter.  (Not to be outdone, Rufus will soon be issuing his own box set; at 19 discs covering 12 odd years, it outweighs his father’s!)

LW3’s own youth is addressed in the tender, sad “School Days,” as he catalogues his high school successes while staring the promise of youth straight in the eyes, and “The Picture,” drawing inspiration from a 40-year old photograph of Loudon and his sister.  The former is the very first track on the box set, dating from 1970. “The Picture” is from 1992’s appropriately-titled History, a set produced with Jeffrey Lesser, a frequent collaborator of another idiosyncratic artist, Rupert Holmes.  “Westchester County,” from 1983, is another nakedly autobiographical visit to the singer’s formative years.  Perhaps the most affecting song in the entire box, however, is “Your Mother and I,” an emotional story written when Loudon and Suzzy Roche were breaking up, and directed at child Lucy (“Your mother and I are not getting along/Somehow, somewhere something went wrong”) in plain-spoken terms.   “Bein’ a Dad” is similarly direct, and the breastfeeding ode “Rufus is a Tit Man” is aired on the DVD via a BBC performance from 2005.

Those looking for the overtly comical side of the songwriter won’t be disappointed.  There’s the deathless “Dead Skunk,” which Wainwright writes was the recipient of praise from none other than Bob Dylan: “Man, that skunk song is pretty good.”  Can’t you just hear Dylan now?  Another quasi-novelty is “IWIWAL”, or “I Wish I Was a Lesbian,” a ludicrous hoedown that’s as infectious as “Thank God I’m a Country Boy!”  Wainwright recorded 1993’s Career Moves at New York’s late, lamented Bottom Line, from which “Tip That Waitress” comes (“The cook is on qualuudes, the busboy deals pot/If she had a real job, she’d quit on the spot!”) in typically droll fashion.  “It’s Love and I Hate It” and “Unhappy Anniversary” are both on the nose, with the latter finding the singer crooning, “I cannot count the days and nights that I have thought of you/Since we went separate ways…”  There are spot-on topical observations, too.  Describing a truly “Hard Day on the Planet,” Wainwright dryly quips, “Even Bob Geldof looks alarmingly thin…”

Many of the songs on 40 Odd Years are in a country or folk style of four or five chords.  And so there isn’t a lot of flashy musicianship by the rock elite.  The relatively few special guests are choice, though!  Van Dyke Parks, Jim Keltner, Bill Frisell, Klaus Voormann, Kate McGarrigle and The Roches all appear on the audio portion of the set, and Rufus, Martha and Lucy duly appear with their father on the DVD.  With the aid of his musicians and sympathetic producers, the subversive songwriter manages to turn country and folk traditions upside down, too.  “Uptown” is an oddly uplifting protest song from 1970, and “I’d Rather Be Lonely” offers a misanthropic credo:  “Love is for the bees and birds/Not for a human being like me/I’d rather be lonely.”

Best of all is “The Man Who Couldn’t Cry,” a darkly hilarious spin on very familiar C&W clichés.  Think of Jerry Jeff Walker’s “Mr. Bojangles” taken to the next level, and you’ll have an idea of this deliciously maudlin allegory that Wainwright admits in the liner notes was unusual for him as it wasn’t rooted in reality.  Producer Richard Thompson, no slouch in the songwriting department himself, added a rockabilly tinge to 1985’s “I’m Alright” from the album of the same name.  The most uncharacteristic songs are those from Wainwright’s two Arista albums from 1976 and 1978 which applied a glossy rock backing to his otherwise-unchanged delivery.  The band Slow Train backed the singer on “Summer’s Almost Over” a slick, seventies track with tinkling piano and vibes.  Wainwright and Apatow have left off the most controversially satiric songs from this period, including “Bicentennial,” a dark and cynical celebration of American heroes (!) like Jack Ruby, and “California Prison Blues” which invokes Charles Manson and Squeaky Fromme.  The attitude adopted on these songs couldn’t have been more “rock,” ironically!

One of Wainwright’s acclaimed songs, “Motel Blues,” is heard in live version on Disc Three, taken from 2008’s Recovery.  This brutal but unflinchingly honest song in which the singer tries to convince a girl in his hotel room to spend the night in exchange for a song on his next LP undoubtedly rang true for many musicians listening to it.  In the hands of a lesser artist, a song like “Motel Blues” might come off as glib, but in Wainwright’s hands, it’s a keenly-observed, regretful slice of life on the road.  He drew on another personal experience for “Samson and the Warden,” in which he’s arrested for marijuana charges and begs the warden not to cut his hair and beard! (Wainwright was busted for possession of the drug in Oklahoma, apparently not the most forgiving of states in his estimation.)

The grab-bag Disc Four of 40 Odd Years compiles various odds and ends, and it’s a strong enough collection to warrant its own release.  The prize for Most Bizarre Track goes to a duet with Barry Humphries as Dame Edna Everage on C. Carson Parks’ “Something Stupid,” a chart-topping duet for Frank and Nancy Sinatra.  It’s every bit as strange as it sounds, possums.  On the other end of the spectrum is a simple, spare version of Frank Loesser’s “More I Cannot Wish You” from Guys and Dolls.  Wainwright’s gentle reading of the song makes it sound like a rustic folk ballad, which affirms the heart and craft of both Loesser and Wainwright.  Also from the stage comes “Florida,” written by LW3 in 2008 for a U.K. theatrical adaptation of Carl Hiassen’s novel Lucky You.  There’s an amusing rewrite of “Santa Claus Is Coming To Town” with the titular jolly old man replaced by Newt Gingrich, and “Surfin’ Queen,” a perverse mid-80s pastiche of a doo-wop death disc that could have made Frank Zappa proud!  There are a few demos, including a rockabilly ode to drumming (“That Cat”) pitched to Ringo Starr and one (“Your Eyes”) intended for the Apatow-written Walk Hard: The Dewey Cox Story.  The lovely, elegiac “No Sure Way” was recorded one week after September 11, 2001, and “Hank and Fred” (about Messrs. Williams and Rogers, of the Neighborhood) is equally touching.

The lengthy DVD draws on a variety of sources, so props to the compilers (and licensing department, natch) for bringing together clips from Austin City Limits, Saturday Night Live, PBS Soundstage, McCabe’s Guitar Shop, The Mike Douglas Show, Nightline and the BBC, among other sources.   This disc includes many of the favorites omitted from the audio portion, like “One Man Guy,” “Unrequited to the Nth Degree” and “Rufus is a Tit Man.”

One of our favorite writers here at The Second Disc, David Wild, provides a customarily amusing and illuminating essay alongside an introduction by Judd Apatow and various thoughts, reflections, apologies and the like from LW3 himself.  There’s a complete album discography with recording personnel and cover artwork for each title, and a good amount of photographs and memorabilia, too.

Loudon Wainwright III is a difficult artist to classify.  The best of his music is both simple and sophisticated, bringing together strains from folk, country, blues, the American popular songbook and rock.  But if you subscribe to the belief that there are only two kinds of music – good music and bad music – Wainwright’s work comfortably falls into the former category.  So let’s imagine a sticker on the shrinkwrap of the box set: “For Fans of Randy Newman, Bob Dylan, John Prine, Steve Goodman, Jimmie Rodgers, Richard Rodgers and Weird Al Yankovic.”  Do check out 40 Odd Years, and drink with me to the next four decades which, with any luck, will be equally odd.